Trimethylsilylacetylene → HCID 57656566, compound

HRID 911560Notes

Reaction equation

HRID 911560 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[CH3:27][Si:28]([CH3:32])([CH3:31])[C:29]#[CH:30]>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:30]#[C:29][Si:28]([CH3:32])([CH3:31])[CH3:27]

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 57656566HCID 57656566, compoundYield 81%

Procedure

Use a method similar to the General Procedure 3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (425 mg, 1 mmol) with 2-trimethylsilylacetylene (0.28 mL, 2 mmol). Purify by chromatography on silica gel eluting with isohexane/EtOAc (100:0 to 85:15 gradient over 40 min) to give the desired intermediate (247 mg, 81%). MS (ES+) m/z: 306 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel eluting with isohexane/EtOAc (100:0 to 85:15 gradient over 40 min)

Sources & evidence

ORD record
ord-4c17b6b369e54ef08a55f47dff1803fc
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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